


And If I Win

by AnotherSPNfanfic



Category: Supernatural
Genre: F/M, Fluff, Third Person POV
Language: English
Status: Completed
Published: 2020-08-03
Updated: 2020-08-03
Packaged: 2021-03-05 21:08:08
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,794
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25681789
Author URL: https://archiveofourown.org/users/AnotherSPNfanfic/pseuds/AnotherSPNfanfic
Summary: Dean meets a girl in a bar. What happens when they run into each other a second time? Written for SPN Dean Bingo and SPN Quote Bingo.
Relationships: Dean Winchester/Original Female Character(s), Dean Winchester/Reader
Comments: 8
Kudos: 34





	And If I Win

Dean pulled into the parking lot of the small dive bar. He put Baby in park and quickly got out. He was halfway across the parking lot when he hollered. “Hurry up, Sam!”

Sam caught up to him as he opened the heavy, wooden door. “A few beers, a couple games of pool, and we’re leaving. We should be researching, Dean.”

“You really know how to have fun, Sammy.” Dean rolled his eyes. “We have been researching for weeks. Maybe a night off will help. Fresh eyes or whatever.”

“This job _was_ the time off.” Sam scoffed and walked over to an empty table.

Dean went straight to the bar and ordered two beers. He glanced around the room as he waited. He noticed a group of frat guys gathered around the pool tables; easy marks, he thought. He also spotted a couple of older gentlemen at the end of the bar, likely regulars you could find there on any given night. Finally, he noticed the woman sitting alone in a dark, corner booth.

She looked deep in thought as she twirled her straw around in her drink. He couldn’t make out much more with her long hair concealing most of her face.

“That’ll be 4.50,” the bartender stated, breaking Dean from his thoughts.

He tossed cash on the bar top as he grabbed the bottles. He glanced toward her once more as he walked over and sat across from his brother.

~

She was halfway through her second drink when the door swung open and two tall, handsome, flannel-wearing guys walked in. Sam and Dean Winchester, she was pretty sure. She’d spotted them—or rather their unmistakable Impala—outside her motel two days earlier. Therefore, that had to be them. It was the middle of nowhere; how many guys could fit the description?

She had rolled into town in search of her sixth or seventh hunt in a row; she had lost count. She’d planned for this to be the last one before she was going to take a break. That is, until she'd spotted the Winchesters. She took their presence as a sign to start her break early. She had heard enough stories to know she didn’t want to get in their way.

She would have left town immediately if she hadn’t already paid for the motel for the week. So now she was pondering where to go next in the only bar for miles around. She scrolled through a few news articles on her phone while she nursed her drink. When the bartender delivered a refill, she moved on to people-watching. She watched the old guys at the bar chat and laugh. They were having such a good time that she almost wanted to join them. As the drinks flowed freely, the frat guys at the pool tables got progressively worse at sinking shots.

The Winchesters shared the occasional hushed conversation. The shorter-haired of them polished off two beers and two shots while the other slowly nursed a single bottle. Eventually, she saw the short-haired one stand from the table. He ran his hand through his hair to mess it up a bit before stumbling slightly on his way to the pool tables. He waved a couple twenties as a greeting.

She was careful not to stare as she watched him swindle the clueless frat guys. She watched the way he glanced at his opponent before intentionally missing a shot. The way he quickly lured them into a sense of superiority. Then, she watched as he upped the bet beyond the cash they had on hand and promptly destroyed them. He was good.

She stood from her table as the guys started throwing a fit. She tossed her hair up into a messy bun as she heard, “You hustled us, asshole.”

“It was just a lucky game. I swear.”

The taller, longer-haired brother walked over to the table. He looked annoyed that he might be stepping into a fight. “Seriously, Dean?”

“I’ll play,” she stated, effectively distracting everyone from the impending brawl. She wandered over to the cue rack on the wall. She pulled one out before turning. “If I win, you give the kid back his watch and you buy me a drink.”

“I’ll buy you a drink,” one of the frat guys offered.

She raised an eyebrow. “Uh, no. Nice try, though.”

The Winchester brother she now knew to be Dean stared at her intensely for a few seconds. He handed the watch over to its rightful owner with an order to get lost. He watched as they all moved over to an empty table across the bar. He raised his chin as if he was sizing her up. “And if I win?”

“You won’t.” She smiled and set to racking the balls. She slid the cue ball into place moments later. She winked at Dean before she broke, pocketing three balls.

Less than five minutes later, she had cleared the table of solids and was announcing, “Eight ball, side pocket.” She couldn’t help but laugh at the looks on both of the Winchester brothers’ faces after she’d won.

“Holy crap. Where’d you learn how to play?” Dean asked.

“I spend a lot of time in back-woods dive bars. I’ll take a whiskey on the rocks, and not the cheap crap.”

Dean smiled. “Yes, ma’am.” He went over to the bar to get drinks. He came back a minute later and handed her a lowball glass. “Will you join us? I’m Dean, by the way. This is Sam.”

She introduced herself as they slid into the same booth the brothers had claimed when they arrived. She took a sip of the whiskey and hummed in satisfaction. “Damn, that’s smooth.”

“Johnny Walker Blue. Bet is a bet and you said no cheap stuff.” Dean shrugged. “Honestly, I am a little shocked this place stocks it.”

She smiled at him. “I’m certainly not gonna complain.”

“So, you said you spend a lot of time in places like this. You do a lot of traveling?” Dean asked.

She nodded, sipping her drink. “Quite a bit, yeah.”

He narrowed his eyes slightly as if he was waiting for more. “For work or for fun?”

“I’m something of a drifter. I get bored if I spend too long in one place.” She had no intention of letting on that she knew who they were or that she was also a hunter. “What about you guys?”

“We travel a lot for work,” Dean answered.

She nodded and took another sip of her whiskey. “Sounds interesting.”

They exchanged looks before shifting their focus back to her like they were expecting her to say something else. “That’s it?” Dean questioned. “You’re not going to ask fifteen more questions about what kind of work we do?”

She shook her head. “Work that requires a lot of travel and has you in this hole-in-the-wall bar… I’m pretty sure I don’t want to know.”

“You’re probably not wrong,” Dean said before sipping his drink.

“Well, it was nice meeting you,” Sam told her before giving his brother a smirk. “But, I think I am going to head back to the motel.”

Dean stood to let Sam out and handed over the car keys. He watched as Sam vanished through the same door they’d entered.

Before he could slide back into the booth, she stood. “Wanna play a game of darts? No bets, just for fun.”

He smiled. “You’re on.” He grabbed his whiskey off the table and wandered to a high-top near the dart boards. After setting his drink down, he retrieved the darts from the board and handed one to her.

She set her drink beside his before she tossed the dart and hit the outside circle of the bullseye. She flashed him a cocky smile as she took another sip of her whiskey.

“Not bad.” He moved to the line and tossed his own dart at the board. It hit the bullseye dead center. “But not good enough.” He winked.

“Lucky shot!” she yelled as he moved to grab the darts again.

“Sore loser?” He teased. He promptly threw all three darts, landing them all in the triple twenty section.

She went to pull them off the board and matched his shots keeping them at a tied score. “You didn’t win anything yet. Maybe I wanted to let you go first.”

“Alright, this is too easy.” Dean flashed her a mischievous smirk. “We need shots.” He headed to the bar and returned moments later with a tray. He handed her one before raising his own to cheers. He tossed it back and winced slightly at the burn.

As he handed her another shot, she asked, “Are you trying to get me drunk?” He shrugged. She rolled her eyes and raised the glass, clinking it against his.

He grabbed the darts to take his next turn. He got 95 points and then watched her take her turn. She only scored 38 points and pouted as she turned to face him. “Clearly, you can hold your liquor better than me.”

He chuckled. “You think so?” He grabbed one of the two remaining shots and downed it. “Happy?”

“Maybe.” She nodded towards the board for him to go again. He moved to the line. As he raised his arm to throw, she leaned in close behind him and whispered in his ear, “Don’t miss.”

The dart landed in the triple 20 spot. He smiled as he turned and locked eyes with her. She was only a few inches away. “Maybe you are just my good luck charm.”

She nodded subtly as her gaze dropped momentarily down to his mouth when his tongue peeked out to wet his lip. Next thing she knew, his palm was on her cheek as his fingers curled gently at the back of her neck urging her closer. He leaned in, resting his forehead against hers. She wrapped her arms around his broad shoulders as she rose to her tiptoes and captured his lips in a soft, almost-shy kiss.

In perfect sync, their lips moved together. His other hand came up to rest on the small of her back and he gently pulled her flush against him. She could feel his body heat radiating through the t-shirt that he had under his flannel. Neither knew how long they stayed like that before he pulled away. His eyes swept over her face before he pressed one more quick kiss to her lips. It took her a moment to catch her breath.

“Wow,” she mumbled, the alcohol in her system letting the comment slip. She locked eyes with him again, finally noticing how intensely green they were.

He chuckled and she felt it rumble through his chest. “Wow, yourself. Any chance you want to get out of here?”

“I, uh, don’t do one-night stands,” she forced out, as if she was fighting herself to say so. She glanced down, not wanting to see the disappointment on his face. “It’s my biggest rule.”

His index finger found her chin, forcing her to look back up at him. He smiled softly. “That’s not a bad rule to live by. How about we finish this game and talk a little more?”

She smiled and nodded. He placed a chaste kiss on her forehead as he pulled away to finish his turn. He was so kind and caring that she was truly tempted to break her rule for him.

He scored another 35 points and she suspected he was going easy on her. He retrieved the darts and handed them over. She took a sip of her whiskey, holding the liquid in her mouth for a second before swallowing. “How about if I can make two bullseyes, I win?”

He squinted his eyes at her as he considered it. “You think you can?” he teased.

She tossed one dart, landing it dead center. “Maybe. Winning is pretty good motivation.”

“Well, then, let’s see it.” He moved to stand close behind her, as she had done to him, but stayed silent. She took an extra moment to aim before throwing. The dart landed high, missing the bullseye by less than half an inch.

“Damn it!” she yelled, catching the attention of everyone in the bar.

Dean tossed his head back as he laughed. She crossed her arms as she tried to hold her glare. He looked back at her just long enough to catch the look and burst into another round of laughter. After another second, she cracked and let out a giggle. 

“I’m sorry,” he started. “You were just so sure you had me beat.”

She punched him lightly on the shoulder. “I would have if you hadn’t given me shots.”

He smiled softly and pulled her closer. He kissed her once more. As he pulled away, he whispered, “Guess we’ll never know.”

She smiled. “What were we talking about?” she asked.

“I think you were saying that you wanted to go sit at the bar and have another round,” he said, a hopeful look in his eyes.

She reached over to grab her drink and finished it off. “Oh, yeah, that’s right. That is a good idea that I had.” He kept his hand on the small of her back as they moved over to the bar top. The bartender approached as they sat on a pair of stools. “Can I get a beer?”

Dean raised two fingers, indicating he would have the same, and set a twenty on the bar. Two bottles were placed in front of them a moment later, followed by his change.

“I think that round was my turn to buy. You did win the darts after all.” She reached to pull out her wallet before Dean grabbed her hand to stop her.

“You said no bets on that game. So you don’t owe me anything. I just wanted to buy a pretty girl a drink.” He winked.

She rolled her eyes and glanced around the mostly empty bar. “Oh, so where is this ‘pretty girl’ you are buying a drink for?”

“She should be here any minute; you mind scooting down a few?” Dean teased. “I wouldn’t want to give her the wrong impression.”

She scooted her stool a few inches closer to him and leaned her head over into his shoulder for just a moment. “How is this?” She smirked as she sat up.

“Perfect.” He smiled as he looked over at her. “How much longer are you planning to be in town?”

She took a drink before answering, “I’m headed out in the morning. I’m thinking I might go and find somewhere to camp for a little while.”

He cringed, almost imperceptibly. “Camping? Like, in a tent out in the middle of the woods?”

“That’s usually what camping involves, yes. Sometimes just sleeping out under the stars is nice, too.” She laughed as a look of complete disgust bloomed across his features. “I take it you are not a fan?”

“I hate camping. Do you know how dangerous it is? How many things might want to try and eat you?” Dean asked.

She played dumb, “You mean like birds, squirrels, and deer?”

“No.” He hesitated before continuing. “More like, uh, bears or wolves.”

She raised an eyebrow. “I have been camping most of my life. I have never had a run-in with any bears or wolves. I have seen a few from a distance, but none that tried to eat me.”

“I guess you’re just lucky then.” He went on to tell a couple stories of the “dangerous wildlife” he had encountered in the past. She was enthralled, trying to decipher what kind of monsters he was talking about. He was being vague enough that she wasn’t quite sure she could guess correctly.

She tried not to laugh when he stumbled over the story as he carefully omitted details. She sipped her beer and listened intently as he finished with a contented smile as he mentioned the people he had saved.

“So, basically, you’re like some kind of real-life Batman?” she joked, despite knowing it was fairly accurate, considering she knew he and his brother had saved the world at least once.

He laughed. “No. I’m not a billionaire.”

She hit the bar with a fist. “Damn. I was so sure you were.”

“Remind me not to bet on your sure things,” he joked.

She finished her beer and glanced toward the door. “This has been so much fun, but I should probably head back to the motel. I really am heading out early tomorrow.”

Dean would have sworn she sounded disappointed. He certainly was. He grabbed her hand gently as he asked, “Stay? Have one last drink, please?”

She nodded, unable to bring herself to say no. “Just one.”

Dean nodded at the bartender to bring them another round. They continued to talk and laugh, and sooner than either would have liked, their drinks were gone.

“Would you let me walk with you?” he asked.

“I appreciate the offer, but if I let you walk with me, I will definitely break my no-one-night-stands rule.” She leaned over and pressed one last kiss to his cheek as she stood.

“ **I bet we will meet again.** ” Dean winked.

She smiled as she looked down to the bar top. “ **You better win that bet, because if we do, that’ll be the end of it.** ”

“ **The end of what?** ” He furrowed his eyebrows.

“ **Life as we know it.** ” She turned and walked across the bar without another word. She smiled back at him quickly before pushing the door open and disappearing through it.

~~ A few weeks later and a few states over ~~

She was on the floor struggling to fight off what she was pretty sure was the last vamp of this nest. She was trying not to panic as she realized she was losing. Suddenly, its head was gone, and it fell limp on top of her. She shoved the body off and stood quickly, ready to keep fighting. As she spun around, she locked on a familiar set of gorgeous green eyes, ones she had thought about so many times over the last few weeks. She noticed Sam behind his brother looking around at the dead vamps on the floor.

“It’s you.” Dean stood slightly slack-jawed for a moment. “You’re a hunter?”

“You took out six vamps on your own?” Sam added.

She couldn’t help but smile at the dumbfounded look on Dean’s face. “Winchesters, thanks for the assist.” She glanced around. “It was eight. There are two in the other room.”

“I never told you our last name.” Dean quirked an eyebrow before realization settled in. “You knew who we were.”

“That beautiful Impala of yours is a bit of a giveaway. Any hunter worth a damn has heard the stories.”

Dean broke eye contact as he tried to hide the shy smile that crossed his face. He looked back up and a frown quickly replaced his smile. “You’re bleeding.” He gestured to his own head, mirroring for her.

She reached up to touch her hairline and winced slightly as she pulled away and looked at her hand. She shrugged. “It’s just a scratch.”

He took a couple steps closer. “May I?”

She didn’t respond, simply tipped her head towards him so he could get a better look. His fingertips ghosted over the skin beside the cut. It felt like sparks running through her at the simple touch.

He pulled away and she instantly missed the contact. “You’re right. It’s not too bad. I can clean it for you, if you’d like.”

“I would appreciate that. It'll be so much easier than trying to do it myself in my rearview mirror.” He turned on his heel to walk outside with her following close behind.

He pulled a first-aid kit from the trunk. “Tell me, sweetheart, you always go running into vamp nests without backup?” He started to dab a disinfectant-soaked gauze pad across the cut, and she hissed at the sting.

“Pretty much, yeah. At this point, I actually prefer it. It is better, and safer, than going in with some stranger who might not be experienced enough. Not everyone has a sibling that can practically read their mind.” She glanced around them. “Speaking of, where is Sam?”

Dean carefully placed three small Steri-strips over her wound. He offered her an ice pack, which she declined. “Starting on the cleanup. You are good to go.” He tossed the kit back into the trunk then turned to face her. “What did you say that night? ‘The end of life as we know it’?”

She nodded slowly.

“How about we start with you not running into vamp nests alone anymore,” he suggested.

“Hmm, are you suggesting I find a hunting partner?” she asked.

He shook his head. “No, I’m volunteering myself.”

She smiled as she stepped closer to him, leaving only a few inches between them. The fingers of her right hand found his left and she intertwined them. He glanced down to her lips for a second before they locked eyes again. “I was really hoping we would run into each other again,” she said quietly.

He leaned in and kissed her. Her hands made their way to the short hairs at the back of his neck. His arms wrapped firmly around her waist, hugging her to him. Sooner than she wanted, he pulled away. He nuzzled his nose against hers. “And I was really hoping I’d get to do that again.”

She nodded her agreement and pulled him into another kiss. He shifted them so he could lean against Baby. She pulled away again when she heard Sam clear his throat behind her.

“You think you guys could help with cleanup first?” he asked once he had their attention.

She mustered up her best puppy eyes. “I thought you guys were here to do that part for me.” She gestured to the small cut Dean had just cleaned. “I hit my head and I just thought you guys could handle it.”

Sam shot her a bitchface. “You said it was just a scratch.”

“Damn. I had to try.” She shrugged. “You guys could at least buy me lunch when we’re done.”

Dean leaned to plant a kiss on her cheek as he moved past her. “I think we can arrange that.”

“Hey, Dean?” She reached out to grab his shoulder before he could get too far away.

He turned back to face her. “Hm?”

Her puppy eyes were back. “Those stories you were telling at the bar… Could you tell me those again with the monster parts?”

“On one condition… You tell me a few of yours.”

She nodded. “I think I can handle that.”

  
  
  



End file.
